Hydrochloric Acid → 3-(Cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid

HRID 1783236

Reaction equation

HRID 1783236 reaction equation
[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([C:15]([N:17]([CH2:21][CH2:22][CH3:23])[CH2:18][CH2:19][CH3:20])=[O:16])[CH:14]=1)[C:7]([O:9]CC)=[O:8])#[N:2].O.[OH-].[Li+].Cl>C(O)C.O>[C:1]([CH2:3][C:4]1[CH:5]=[C:6]([CH:12]=[C:13]([C:15]([N:17]([CH2:18][CH2:19][CH3:20])[CH2:21][CH2:22][CH3:23])=[O:16])[CH:14]=1)[C:7]([OH:9])=[O:8])#[N:2]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 21086102Ethyl 3-(cyanomethyl)-5-[(dipropylamino)carbonyl)benzoate

Product 1

HCID 210857723-(Cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of ethyl 3-[(dipropylamino)carbonyl]-5-(hydroxymethyl)benzoate (1.5 g) and phosphorous tribromide (0.95 mL) is stirred in dichloromethane (10 mL) and heated at 50 degrees C. for 4 hours and then cooled and partitioned between dichloromethane and water. The organic phase is separated and washed with aqueous sodium bicarbonate and then dried over magnesium sulfate and taken to dryness to give ethyl 3-(bromomethyl)-5-[(dipropylamino)carbonyl]benzoate, high resolution MS MH+=370.1020. Ethyl 3-(bromomethyl)-5-[(dipropylamino)carbonyl]benzoate (1.4 g) and sodium cyanide (0.2 g) are stirred in dry DMSO (25 mL) at 20-25 degrees C. for 3.5 hours and the mixture is then partitioned between ethyl acetate, water and saline. The organic layer is separated and dried over magnesium sulfate and taken to dryness under reduced pressure to give ethyl 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoate. Ethyl 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoate (0.6 g) is hydrolyzed with lithium hydroxide monohydrate (0.1 g) in ethanol and water at 20-25 degrees C. overnight and then added to water (50 mL). The pH is adjusted to 4 using concentrated hydrochloric acid and the mixture is partitioned between ethyl acetate, water, and saline. The organic phase is separated and dried over magnesium sulfate and taken to dryness under reduced pressure to give 3-(cyanomethyl)-5-[(dipropylamino)carbonyl]benzoic acid, MS M+H=287.2.

Workup

  1. customthe mixture is partitioned between ethyl acetate, water, and saline
  2. customThe organic phase is separated
  3. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-5abba60dc17c4279a0fabe86a30603c5
Source dataset
uspto-grants-2009_03
Patent number
US07498436B2

Linked notes

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